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Trifluoroacetic acid → 4-Amino-1-[(9S,10S)-2-chloro-9,10-dihydro-9,10-methanoanthracen-9-yl-carbonyl]piperidine

HRID 2209578
ノート
印刷プレビュー

反応式

HRID 2209578 の反応式
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C@:15]23[CH2:30][C@H:22]([C:23]4[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][C:28]=42)[C:21]2[C:16]3=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=[O:35].[OH-].[Na+]>C(Cl)Cl>[NH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([C@:15]23[CH2:30][C@H:22]([C:23]4[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][C:28]=42)[C:21]2[C:16]3=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:35])[CH2:10][CH2:9]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 57094261HCID 57094261、化合物

生成物 1

HCID 572905474-Amino-1-[(9S,10S)-2-chloro-9,10-dihydro-9,10-methanoanthracen-9-yl-carbonyl]piperidine収率 100%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred solution of t-butyl-N-(1-[(9S,10S)-2-chloro-9,10-dihydro-9,10-methanoanthracen-9-ylmethyl]-4-piperidyl)carbamate produced in Example 1b (1.24 g, 2.74 mmol) in methylene chloride (15 mL) was added trifluoroacetic acid (2.11 mL, 27.37 mmol). After stirring the resulting mixture for 18 h, the reaction was concentrated to give a pale pink syrup. The syrup was dissolved in methylene chloride (100 mL), cooled to 0 C. (ice bath) and treated with 3N sodium hydroxide and extracted with methylene chloride (3×50 mL). The combined extracts was washed with 3N sodium hydroxide (2×75 mL) and brine (75 mL), dried (sodium sulfate), filtered, and concentrated to give the title compound as a white foamy glass (967 mg, 100%); mp 93°-5° C.; MS(CI); 353 (M+H); NMR (300 MHz,DMSO-d6): 1.23(br m, 2H), 1.67-1.85(br m, 2H), 2.71-3.02(br m, 5H), 3.27-3.39(br m, part. submerged, 2H), 3.66(br s, 1H), 4.42(s, 1H), 4.47(s, 1H), 7.00(m, 3H), 7.30-7.66(br m, 4H).

後処理

  1. concentrationthe reaction was concentrated
  2. customto give a pale pink syrup
  3. temperaturecooled to 0 C
  4. extractionextracted with methylene chloride (3×50 mL)
  5. washThe combined extracts was washed with 3N sodium hydroxide (2×75 mL) and brine (75 mL)
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-3c250a460bb64abc867473110520abd7
出典データセット
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05455246

反応ノート

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