Benzaldehyde → 4-Benzylamino-cyclohexanecarboxylic acid tert-butyl ester

HRID 444712노트

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HRID 444712 반응식
[C:1]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O-]S([O-])(=O)=O.[Mg+2].[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[BH4-].[Na+]>CO.O>[C:1]([O:5][C:6]([CH:8]1[CH2:9][CH2:10][CH:11]([NH:14][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 240BenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 18698345tert-Butyl 4-aminocyclohexane-1-carboxylate

생성물 1

HCID 687248414-Benzylamino-cyclohexanecarboxylic acid tert-butyl ester수율 100.9%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

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온도
0 °C

실험 절차

To a solution of 4-amino-cyclohexanecarboxylic acid tert-butyl ester (500 mg, 2.500 mmol) in MeOH (3 mL) is added TEA (140 uL, 1.000 mmol), MgSO4 (452 mg, 3.750 mmol), and benzaldehyde (278 uL, 2.750 mmol). The mixture stirs 1 h. The mixture is then cooled to 0° C. and NaBH4 (568 mg, 15.00 mmol) is added portionwise over 10 min. The mixture stirs 1 h at ambient temperature. Then H2O (20 mL) is added and the mixture is extracted with EtOAc (2×50 mL), dried and concentrated to affords 730 mg of 4-benzylamino-cyclohexanecarboxylic acid tert-butyl ester. LC/MS: [M+H]+ 290, Rt=0.80 min (method 6).

후처리

  1. waitThe mixture stirs 1 h at ambient temperature
  2. extractionthe mixture is extracted with EtOAc (2×50 mL)
  3. customdried
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5e9039f2f12d4e88a6cb87c4b568f737
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476224B2

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