Water → (1R,3S,4S)-3-(benzylamino-methyl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

HRID 882794Notes

Reaction equation

HRID 882794 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)[C@@H:20]2[CH2:24][C@H:17]1[CH2:18][CH2:19]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)[C@@H:20]2[CH2:24][C@H:17]1[CH2:18][CH2:19]2)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 18396214(1R,3S,4S)-3-Formyl-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Product 1

HCID 66865917(1R,3S,4S)-3-(benzylamino-methyl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzylamine (49.7 mmol) is added to a solution of (1R,35,45)-3-formyl-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (49.7 mmol) in DCM (200 mL). The mixture is treated with sodium triacetoxyborohydride (69.6 mmol), stirred for additional 20 min, poured into water (200 mL) and stirred vigorously for 10 min. The layers are separated and the aq. layer is extracted twice with DCM (2×100 mL). The combined organic layers are washed with sat. NaHCO3 solution (100 mL), water (100 mL) and brine (150 mL), dried over MgSO4 and treated with activated charcoal (5 g). The mixture is filtered through celite and the filtrate is concentrated in vacuo to give the desired benzylamine which is used without further purification. LC-MS (basic): tR=1.00 min; [M+H]+=317.3.

Workup

  1. stirringstirred vigorously for 10 min
  2. customThe layers are separated
  3. extractionthe aq. layer is extracted twice with DCM (2×100 mL)
  4. washThe combined organic layers are washed with sat. NaHCO3 solution (100 mL), water (100 mL) and brine (150 mL)
  5. dry with materialdried over MgSO4
  6. additiontreated with activated charcoal (5 g)
  7. filtrationThe mixture is filtered through celite
  8. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-df7f30b9ce3144ecbc922a4df094a7c1
Source dataset
uspto-grants-2012_08
Patent number
US08236801B2

Reaction notes

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