Methyl chloroformate → Methyl N-[(1R,3S)-3-benzyloxycarbonylaminocyclohexyl]carbamate

HRID 526948

Reaction equation

HRID 526948 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:3]1.Cl[C:20]([O:22][CH3:23])=[O:21].C(N(CC)CC)C>C1COCC1>[CH2:11]([O:10][C:9]([NH:8][C@H:4]1[CH2:5][CH2:6][CH2:7][C@@H:2]([NH:1][C:20](=[O:21])[O:22][CH3:23])[CH2:3]1)=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 69756715Benzyl ((1S,3R)-3-aminocyclohexyl)carbamate2×

Product 1

HCID 68007620Methyl N-[(1R,3S)-3-benzyloxycarbonylaminocyclohexyl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl N-[(1S,3R)-3-aminocyclohexyl]carbamate, 18e, (0.99 g, 3.99 mmol) was dissolved in THF (20 mL) and treated with methyl chloroformate (0.62 mL, 7.97 mmol), followed by triethylamine (1.67 mL, 11.96 mmol). After stirring for 1 hour at room temperature, the solvent was evaporated under reduced pressure and the residue was diluted into 1:3 mixture of CH2Cl2:EtOAc (130 mL) and washed with 1N HCl (50 mL) and 2N Na2CO3 (50 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford the desired product, 19a, as a white solid (1.09 g, 89% yield).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted into 1:3 mixture of CH2Cl2
  3. washEtOAc (130 mL) and washed with 1N HCl (50 mL) and 2N Na2CO3 (50 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-55bcb3c49562482bb9f7303c3618d05e
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Linked notes

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