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Sodium cyanoborohydride → methyl (7S)-7-[(1-{2-[(tert-butoxycarbonyl)(methyl)amino]ethyl}pyrrolidin-2-yl)methoxy]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

HRID 1669451
ノート
印刷プレビュー

反応式

HRID 1669451 の反応式
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:33]([O:35][CH3:36])=[O:34])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][C@@H:16]([O:26][CH2:27][CH:28]2[CH2:32][CH2:31][CH2:30][NH:29]2)[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:37][N:38]([CH2:46][CH:47]=O)[C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42].[BH3-]C#N.[Na+]>CO.C1COCC1.CC(O)=O>[C:41]([O:40][C:39]([N:38]([CH3:37])[CH2:46][CH2:47][N:29]1[CH2:30][CH2:31][CH2:32][CH:28]1[CH2:27][O:26][C@H:16]1[CH2:15][N:14]2[C:13]3[CH:12]=[C:11]([C:33]([O:35][CH3:36])=[O:34])[CH:10]=[CH:9][C:8]=3[C:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[C:21]2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17]1)=[O:45])([CH3:44])([CH3:43])[CH3:42]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 5003444Sodium cyanoborohydride2 回HCID 10725881tert-butyl N-methyl-N-(2-oxoethyl)carbamate2 回HCID 67345272methyl (7S)-14-cyclohexyl-7-(pyrrolidin-2-ylmethoxy)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

生成物 1

HCID 67344077methyl (7S)-7-[(1-{2-[(tert-butoxycarbonyl)(methyl)amino]ethyl}pyrrolidin-2-yl)methoxy]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 21899815MeOH tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

To a solution (0.02 M) of methyl (7S)-14-cyclohexyl-7-(pyrrolidin-2-ylmethoxy)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate in MeOH/THF (2/1), AcOH (cat.) was added followed by tert-butyl methyl(2-oxoethyl)carbamate (2 eq, prepared as described in Tetrahedron 2002, 58, 1719-1737). The reaction was stirred at RT for 30 min at which point NaCNBH3 (2 eq) was added and the mixture was stirred at 40° C. for 1 h. Additional tert-butyl methyl(2-oxoethyl)carbamate (1 eq) and NaCNBH3 (5 eq) were added and the reaction was stirred for further 30 min at 40° C. The reaction was quenched by adding sat. aq. NaHCO3. The aqueous phase was extracted with EtOAc and the combined organics washed with brine before being dried (Na2SO4), filtered and concentrated in vacuo. The product was used in the subsequent step without further purification. (ES+) m/z 646 (M+H)+

後処理

  1. additionwas added
  2. stirringthe reaction was stirred for further 30 min at 40° C
  3. customThe reaction was quenched
  4. additionby adding sat. aq. NaHCO3
  5. extractionThe aqueous phase was extracted with EtOAc
  6. washthe combined organics washed with brine
  7. dry with materialbefore being dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe product was used in the subsequent step without further purification

出典と根拠

ORDレコード
ord-02155ec66ca24895b80eacf1fe381c50
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07989438B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート