Sodium borohydride → 5-(R)-(2-(S)-Amino-1-(S)-hydroxy-3-phenylpropyl)-2-(S)-(2-cyclohexylethyl)-morpholine-4-carboxylic acid tert-butyl ester

HRID 20371

반응식

HRID 20371 반응식
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([C@@H:14]([OH:26])[C@@H:15]([N+:23]([O-])=O)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][O:11][C@@H:10]([CH2:27][CH2:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.[Ni](Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([C@@H:14]([OH:26])[C@@H:15]([NH2:23])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][O:11][C@@H:10]([CH2:27][CH2:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 4311764Sodium borohydride2회HCID 685582042(S)-(2-Cyclohexylethyl)-5-(R)-(1-(R)-hydroxy-2-(S)-nitro-3-phenylpropyl)-morpholine-4-carboxylic acid tert-butyl ester

생성물 1

HCID 685618115-(R)-(2-(S)-Amino-1-(S)-hydroxy-3-phenylpropyl)-2-(S)-(2-cyclohexylethyl)-morpholine-4-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 24385Nickel Dichloride촉매HCID 887Methanol용매

실험 절차

Dissolve 2(S)-(2-cyclohexylethyl)-5-(R)-(1-(R)-hydroxy-2-(S)-nitro-3-phenylpropyl)-morpholine-4-carboxylic acid tert-butyl ester (152 mg, 0.32 mmol) in methanol (5 mL), and place in a room temperature oil bath. Add dry nickel (II) chloride (62 mg, 0.48 mmol) followed by sodium borohydride (30 mg, 0.80 mmol). After 3 minutes add a second portion of sodium borohydride (30 mg, 0.80 mmol). Quench with water (1 mL) then 0.1 N sodium hydroxide (3 mL). Dilute with ethyl acetate and extract (3×30 mL). Wash the combined extracts with saturated aqueous sodium chloride, filter through a pad of Celite®, dry (sodium sulfate) and concentrate to give the desired compound as a white solid which is used without further purification (140 mg, 99%).

후처리

  1. customQuench with water (1 mL)
  2. additionDilute with ethyl acetate
  3. extractionextract (3×30 mL)
  4. washWash the combined extracts with saturated aqueous sodium chloride
  5. filtrationfilter through a pad of Celite®
  6. dry with materialdry (sodium sulfate)
  7. concentrationconcentrate

출처 및 근거

ORD 기록
ord-e2c3e29e95d6444e96f3a7928cc9d467
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745438B2

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