Acetic Acid → (S)-tert-butyl 4-((2-hydroxy-2-methyl-1-phenylpropyl)amino)piperidine-1-carboxylate

HRID 525415Notes

Reaction equation

HRID 525415 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(O)(=O)C.[NH2:19][C@@H:20]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:21]([CH3:24])([OH:23])[CH3:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[OH:23][C:21]([CH3:24])([CH3:22])[C@@H:20]([NH:19][CH:11]1[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 46941324(S)-1-amino-2-methyl-1-phenylpropan-2-ol

Product 1

HCID 89814223(S)-tert-butyl 4-((2-hydroxy-2-methyl-1-phenylpropyl)amino)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flask charged with boc-4-piperidone (2.412 g, 12.10 mmol, Alfa-Aesar) was added DCM (60.5 mL), acetic acid (0.901 mL, 15.74 mmol), (S)-1-amino-2-methyl-1-phenylpropan-2-ol (2 g, 12.10 mmol, BOC Scientific) and sodium triacetoxyborohydride (3.59 g, 16.95 mmol) respectively. The resulting orange suspension was stirred at room temperature for 3 h. LCMS indicated good conversion to desired product. To the mixture was added saturated NaHCO3 and K2CO3 pellets. The mixture was transferred to a separatory funnel and extracted with DCM (2×). The combined organics were dried with Na2SO4, filtered, and dried under reduced pressure. The material thus obtained was used without further purification.

Sources & evidence

ORD record
ord-fe0473dd018e4e2284c5bffe46616dff
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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