Sodium triacetoxyborohydride → tert-butyl (2S,3R)-3-hydroxy-4-(3-(2-hydroxypropan-2-yl)benzylamino)-1-phenylbutan-2-ylcarbamate

HRID 2071184ノート

反応式

HRID 2071184 の反応式
[NH2:1][CH2:2][C@@H:3]([OH:20])[C@@H:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH:21][C:22]([C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH:28]=O)([CH3:24])[CH3:23].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.CCOC(C)=O>[OH:20][C@H:3]([CH2:2][NH:1][CH2:28][C:27]1[CH:30]=[CH:31][CH:32]=[C:25]([C:22]([OH:21])([CH3:23])[CH3:24])[CH:26]=1)[C@@H:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

6

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 10333883tert-butyl (2S,3R)-4-amino-3-hydroxy-1-phenylbutan-2-ylcarbamateHCID 866474433-(2-Hydroxypropan-2-yl)benzaldehyde

生成物 1

HCID 59569847tert-butyl (2S,3R)-3-hydroxy-4-(3-(2-hydroxypropan-2-yl)benzylamino)-1-phenylbutan-2-ylcarbamate収率 65.4%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of tert-butyl (2S,3R)-4-amino-3-hydroxy-1-phenylbutan-2-ylcarbamate (230 mg, 0.82 mmol) in THF was added 3-(2-hydroxypropan-2-yl)benzaldehyde (180 mg, 01.06 mmol) and stirred for 30 min at room temperature, NaB(OAc)3H (302.5 mg, 1.43 mmol) was then added portionwise in 30 min, and the resulting mixture was stirred at the same temperature overnight. The reaction mixture was diluted with EtOAc, and washed with saturated aqueous NaHCO3. The organic layer was separated and dried (Na2SO4). Concentration in vacuo, followed purification with flash chromatography to give the desired product as a white solid (230 mg, 65% yield). 1H NMR (CDCl3): d: 8.514 (m, 2H), 7.717 (s, 1H), 7.321-7.203 (m, 5H), 3.831 (s, 3H), 3.580 (m, 1H), 2.978 (m, 1H), 2.890-2.755 (m, 3H), 1.724 (d, J=11.1 Hz, 6H), 1.364 (s, 9H).

後処理

  1. stirringthe resulting mixture was stirred at the same temperature overnight
  2. washwashed with saturated aqueous NaHCO3
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationConcentration in vacuo
  6. custompurification with flash chromatography

出典と根拠

ORDレコード
ord-e1f571036896470381c1ed9aa15feaec
出典データセット
uspto-grants-2012_10
特許番号
US08299267B2

反応ノート

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