Sodium Carbonate → HCID 68764885, compound

HRID 1171600Notes

Reaction equation

HRID 1171600 reaction equation
N[C@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@H:3]1[CH2:15][OH:16].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>C(Cl)Cl>[CH2:27]([O:26][C:24]([C@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@@H:3]1[CH2:15][OH:16])=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 68769736HCID 68769736, compound

Product 1

HCID 68764885HCID 68764885, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A sample of (3R,4S)-tert-butyl 4-amino-3-(hydroxymethyl)piperidine-1-carboxylate (113.6 mMol) was dissolved in CH2Cl2 prior to the addition of saturated sodium carbonate (180 mL). This mixture was cooled to 0° C. and then benzyl chloroformate (21.76 mL, 136.32 mMol) was added slowly. The cooling was removed and stirring continued overnight. Partitioned the mixture between water and CH2Cl2. Aqueous layer was re-extracted with CH2Cl2. Combined organic layer was washed with brine and dried (MgSO4). Filtered, concentrated and dried in vacuo to get the desired product, (3R,4S)-tert-butyl 4-(benzyloxycarbonyl)-3-(hydroxymethyl)piperidine-1-carboxylate as a yellow oil.

Workup

  1. customThe cooling was removed
  2. customPartitioned the mixture between water and CH2Cl2
  3. extractionAqueous layer was re-extracted with CH2Cl2
  4. washCombined organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationFiltered
  7. concentrationconcentrated
  8. customdried in vacuo

Sources & evidence

ORD record
ord-fc880e3cc01f4d1d842c41abe237a585
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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