Water → (1S,3S,5S)-3-(b enzylamino-methyl)-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

HRID 2064791Notes

Reaction equation

HRID 2064791 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:13][C:14]([N:16]1[C@H:21]([CH:22]=O)[CH2:20][C@H:19]2[C@@H:17]1[CH2:18]2)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>C(Cl)Cl>[C:9]([O:13][C:14]([N:16]1[C@H:21]([CH2:22][NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:20][C@H:19]2[C@@H:17]1[CH2:18]2)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 58278672tert-butyl (1S,3S,5S)-3-formyl-2-azabicyclo[3.1.0]hexane-2-carboxylate

Product 1

HCID 67081441(1S,3S,5S)-3-(b enzylamino-methyl)-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzylamine (17.5 mmol, 1.0 eq) is added to a solution of (1S,3S,5S)-3-formyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (17.5 mmol, 1.0 eq) in DCM (100 mL). The mixture is treated with sodium triacetoxyborohydride (24.5 mmol, 1.4 eq), stirred for additional 14 h, poured into water (200 mL) and stirred vigorously for 10 min. The layers are separated and the aqueous layer is extracted twice with DCM (2×100 mL). The combined organic layers are washed with sat. NaHCO3 solution (100 mL) and water (100 mL), dried over Na2SO4 and concentrated in vacuo to give the desired benzylamine as a brownish oil which is used without further purification. LC-MS (basic): tR=0.96 min; [M+H]+=303.3.

Workup

  1. stirringstirred vigorously for 10 min
  2. customThe layers are separated
  3. extractionthe aqueous layer is extracted twice with DCM (2×100 mL)
  4. washThe combined organic layers are washed with sat. NaHCO3 solution (100 mL) and water (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-378be2f95ef447ad8390514674027f9f
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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