(Phenylmethoxy)acetaldehyde → HCID 178525080, compound

HRID 491877Notes

Reaction equation

HRID 491877 reaction equation
[CH2:1]([O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@@H:14]([NH2:17])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([O:25][CH2:26][CH:27]=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH2:1]([O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@@H:14]([NH:17][CH2:27][CH2:26][O:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 108989(Phenylmethoxy)acetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178511568HCID 178511568, compound

Product 1

HCID 178525080HCID 178525080, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of cis-4-amino-cyclohexanecarboxylic acid benzyl ester (8 g, 34 mmol) and benzyloxyacetaldehyde (4.8 mL, 34 mmol) in 1,2-dichloroethane (2 L), was stirred at room temperature overnight. Then NaBH(OAc)3 (11 g, 51 mmol) was added and the reaction mixture was stirred at room temperature for 2 hours. Most of the solvent was then removed by vacuum. EtOAc (1 L) was added, and the resulting solution as washed with brine. The organic layer was dried over MgSO4, filtered, and evaporated to yield a residue. The residue was purified by column chromatography with flash silica gel (1:1 heptane/EtOAc) to yield cis-4-(2-benzyloxy-ethylamino)-cyclohexanecarboxylic acid benzyl ester as an oil.

Workup

  1. customMost of the solvent was then removed by vacuum
  2. additionEtOAc (1 L) was added
  3. washthe resulting solution as washed with brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto yield a residue
  8. customThe residue was purified by column chromatography with flash silica gel (1:1 heptane/EtOAc)

Sources & evidence

ORD record
ord-ec3421a9a983457884dfa3b5b404f698
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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