Ammonia → (1R,3S)-3-(Boc-amino)cyclohexanecarboxamide

HRID 1257715노트

반응식

HRID 1257715 반응식
C(OC(Cl)=O)C(C)C.[C:9]([O:13][C:14]([NH:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH:19]([C:23]([OH:25])=O)[CH2:18]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C[N:27]1CCOCC1.N>C1COCC1>[C:9]([O:13][C:14](=[O:15])[NH:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH:19]([C:23](=[O:25])[NH2:27])[CH2:18]1)([CH3:12])([CH3:11])[CH3:10]

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 44203163-(((Tert-butoxy)carbonyl)amino)cyclohexane-1-carboxylic acid

생성물 1

HCID 67324654(1R,3S)-3-(Boc-amino)cyclohexanecarboxamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Isobutylchloroformate (2.06 g, 15.0 mmol) was added dropwise with cooling in an ice-methanol bath to a solution of 3-tert-butoxycarbonylamino-cyclohexanecarboxylic acid (3.15 g, 13.0 mmol) and N-methylmorpholine (1.52 g, 15.0 mmol) in THF (40 mL). After stirring for 30 mins, methanolic ammonia (7M, 5 mL) was added. The mixture was allowed to warm to room temperature, and left to stand overnight. The residue remaining on evaporation of solvent was partitioned between aq. NH4Cl (150 mL) and DCM (150 mL). The solid suspended in the organic layer was collected, the filtrate evaporated, and the combined solids crystallised from methanol to afford 2.07 (66%) of (3-carbamoyl-cyclohexyl)-carbamic acid tert-butyl ester as colourless plates. 1H NMR (400 MHz, MeOD) δ: 6.65-6.59 (m, 1H), 3.40-3.28 (m, 1H), 2.35-2.23, (m, 1H), 2.01-1.92 (m, 1H), 1.91-1.80 (m, 2H), 1.80-1.71 (m, 1H), 1.42 (s, 9H), 1.40-1.21 (m, 3H), 1.19-1.05 (m, 1H).

후처리

  1. waitleft
  2. waitto stand overnight
  3. customThe residue remaining on evaporation of solvent
  4. customwas partitioned between aq. NH4Cl (150 mL) and DCM (150 mL)
  5. customwas collected
  6. customthe filtrate evaporated
  7. customthe combined solids crystallised from methanol

출처 및 근거

ORD 기록
ord-3e47cc688fb7499eb2fdfec9c1c73b7f
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461328B2

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