Benzyl chloroformate → (S)-1-Boc-3-(Cbz-amino-methyl)-piperidine

HRID 1081202Notes

Reaction equation

HRID 1081202 reaction equation
[OH-].[Na+].[NH2:3][CH2:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1.Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC.O>[CH2:22]([O:21][C:19]([NH:3][CH2:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1)=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 1502022tert-Butyl (3S)-3-(aminomethyl)piperidine-1-carboxylate

Product 1

HCID 45158795(S)-1-Boc-3-(Cbz-amino-methyl)-piperidine

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

A)a) 3.7 g of tetrabutylammonium hydrogen sulphate and 100 ml of 1N sodium hydroxide solution are added to a solution of 10.0 g of t-butyl (S)-3-aminomethyl-1-piperidinecarboxylate (Example 6d) in 400 ml of hexane and 100 ml of water. 9.3 ml of benzyl chloroformate are added dropwise to this mixture and the mixture obtained is stirred at room temperature for 3 hours. Subsequently, the organic phase is separated, washed with water, 10% citric acid, water and saturated sodium bicarbonate solution, dried and evaporated. t-Butyl (S)-3-[(1-(benzyloxy)formamido]-methyl]-1-piperidinecarboxylate is obtained.

Workup

  1. customthe mixture obtained
  2. customSubsequently, the organic phase is separated
  3. washwashed with water, 10% citric acid, water and saturated sodium bicarbonate solution
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-ad788f67bec64e588c82904a4ac2c36a
Source dataset
uspto-grants-1996_12
Patent number
US05583133

Reaction notes

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