Benzaldehyde → (3S,4R)-3-benzylaminomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidine

HRID 859898노트

반응식

HRID 859898 반응식
[NH2:1][CH2:2][C@@H:3]1[C@@H:7]([F:8])[CH2:6][N:5]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:4]1.NCC1CN(C(O[CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=O)CC=1.C(=O)C1C=CC=CC=1.Cl.[OH-].[Na+]>CO>[CH2:29]([NH:1][CH2:2][C@@H:3]1[C@@H:7]([F:8])[CH2:6][N:5]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:4]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

참가 물질

7

반응물 5

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 230620723-Aminomethyl-1-benzyloxycarbonyl-3-pyrrolineHCID 66705221(3S,4R)-3-aminomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidine

생성물 1

HCID 66704865(3S,4R)-3-benzylaminomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidine

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture (310 mg) of (3S,4R)-3-aminomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidine and 3-aminomethyl-1-benzyloxycarbonyl-3-pyrroline was dissolved in methanol (4 mL). To this solution, molecular sieves 4A (130 mg) and benzaldehyde (0.13 mL) were sequentially added and the mixture was stirred at room temperature for 1 hour. Subsequently, a borane-pyridine complex (0.19 mL) was added and the mixture was further stirred at room temperature for 4 hours. This was followed by addition of 6 mol/L hydrochloric acid (2 mL) and stirring at room temperature for 1 hour. Subsequently, a 30% aqueous solution of sodium hydroxide was added to make the mixture basic and the mixture was extracted with diethyl ether (3×10 mL). The diethyl ether extracts were combined and the combined diethyl ether layer was concentrated under reduced pressure. The resulting residue was purified on a silica gel column (eluant=dichloromethane: methanol=10:1) to give 177 mg of (3S,4R)-3-benzylaminomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidine as a pale yellow oil.

후처리

  1. additionSubsequently, a borane-pyridine complex (0.19 mL) was added
  2. stirringthe mixture was further stirred at room temperature for 4 hours
  3. stirringstirring at room temperature for 1 hour
  4. extractionthe mixture was extracted with diethyl ether (3×10 mL)
  5. concentrationthe combined diethyl ether layer was concentrated under reduced pressure
  6. customThe resulting residue was purified on a silica gel column (eluant=dichloromethane: methanol=10:1)

출처 및 근거

ORD 기록
ord-5bc1aff3d99741a0b59de677506cec59
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153851B2

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