Benzaldehyde → HCID 69819234, compound

HRID 1006328Notes

Reaction equation

HRID 1006328 reaction equation
Cl.[CH3:2][O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][CH2:8][NH:7]1)=[O:5].C(N(CC)C(C)C)(C)C.[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCl>[CH3:2][O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][CH2:8][N:7]1[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:5]

Participants

7

Reactant 5

HCID 240BenzaldehydeHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 13246232methyl (2S)-piperidine-2-carboxylate hydrochloride

Product 1

HCID 69819234HCID 69819234, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S)-Piperidine-2-carboxylic acid methyl ester hydrochloride (625 mg) was dissolved in dichloromethane. Then N,N-diisopropylethylamine (0.91 ml) and benzaldehyde (0.53 ml) were added to the solution at 0° C. After the whole was stirred for 30 minutes at the same temperature, sodium triacetoxyborohydride (1.48 g) was added. The reaction mixture was allowed to room temperature and stirred for 3 hours. The mixture was poured into aqueous saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated under reduced pressure to give (2S)-1-benzylpiperidine-2-carboxylic acid methyl ester (795 mg).

Workup

  1. additionwas added
  2. customwas allowed to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over magnesium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4ecc2fa5adaf41b2a186701f65308ae0
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

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