Phenylacetaldehyde → HCID 57183740, compound

HRID 264687Notes

Reaction equation

HRID 264687 reaction equation
[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([NH2:14])[CH2:11][CH2:10][N:9]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]1([CH2:28][CH:29]=O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([BH3-])#N.[Na+].C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([NH:14][CH2:29][CH2:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:11][CH2:10][N:9]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 998PhenylacetaldehydeHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 21970305HCID 21970305, compound

Product 1

HCID 57183740HCID 57183740, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1 g (3.44 mmol) of (2R*,4S*)-2-benzyl-1-t-butyloxycarbonyl-4-piperidinamine is reacted in analogy to Example 11a with 1 ml (4.48 mmol) of phenylacetaldehyde, 0.433 g (6.89 mmol) of sodium cyanoborohydride, 0.791 g (9.64 mmol) of sodium acetate and 434 μl of acetic acid to give the title compound (805 mg, 60%). TLC:methylene chloride/methanol/cone. ammonia (700:50:1) Rf =0.35, FD-MS:M+ =394.

Sources & evidence

ORD record
ord-6ab2de10325e4fcc99ca6e12b98cfd4c
Source dataset
uspto-grants-1997_07
Patent number
US05646144

Reaction notes

Loading…