Sodium Carbonate → Benzyl carbamate

HRID 1468188Notes

Reaction equation

HRID 1468188 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:15][C:16](=[O:18])[NH2:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([BH3-])#N.[Na+].C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C>[CH2:8]([O:15][C:16](=[O:18])[NH2:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 86672753HCID 86672753, compound

Product 1

HCID 12136Benzyl carbamateYield 87.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

Add (S)-6-amino-4,5,6,7-tetrahydro-benzothiazol-2-yl)-carbamic acid benzyl ester trifluoroacetate (0.10 g, 0.24 mmol) to the dialdehyde solution. Adjust the pH of the solution to 4 by adding a few drops of acetic acid and is stir for 30 min. Add sodium cyanoborohydride (0.15 g, 2.40 mmol) and stir the mixture stirred for 16 h at room temperature. Neutralize the solution by addition of Na2CO3 and extract with CH2Cl2. Dry the organic layer is with MgSO4 and concentrate. Purify the residue with column chromatography eluting with 5-100% CH2Cl2/20% MeOH/1% NH4OH to give (S)-6-piperidin-1-yl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-carbamic acid benzyl ester (0.08 g, 0.21 mmol).

Workup

  1. stirringstirred for 16 h at room temperature
  2. extractionextract with CH2Cl2
  3. customDry the organic layer
  4. concentrationconcentrate
  5. customPurify the residue with column chromatography
  6. washeluting with 5-100% CH2Cl2/20% MeOH/1% NH4OH

Sources & evidence

ORD record
ord-bbbac338c53842e5987dbdef0773825b
Source dataset
uspto-grants-2015_04
Patent number
US09000154B2

Reaction notes

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