Water → Phenylmethyl 3-amino-3-methyl-1-piperidinecarboxylate

HRID 1257748Notes

Reaction equation

HRID 1257748 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C:13]([C:18](=O)N)(C)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(=O)OI(C1C=CC=CC=1)OC(C(F)(F)F)=O.O.C(#[N:45])C>>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C:13]([NH2:45])([CH3:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 67324533Phenylmethyl 3-(aminocarbonyl)-3-methyl-1-piperidinecarboxylate

Product 1

HCID 67323689Phenylmethyl 3-amino-3-methyl-1-piperidinecarboxylateYield 93%

Conditions

Temperature
25 °C

Procedure

3-Carbamoyl-3-methyl-piperidine-1-carboxylic acid benzyl ester (500 mg, 1.81 mmol) in acetonitrile (10 mL) was treated with [bis(trifluoroacetoxyl)iodo]benzene (PIFA) (800 mg, 1.86 mmol) and water (2 mL), the mixture was allowed to stir at 25° C. for 3 hours. LCMS showed starting material consumed, the mixture was heated to 70° C. for 30 min to decompose excess PIFA. The mixture was purified by column chromatography (eluting with 30˜50% methanol in dichloromethane) to give 420 mg (93%) of 3-Amino-3-methyl-piperidine-1-carboxylic acid benzyl ester. LCMS (Method K, ESI): RT=0.95 min, m+H=249.0.

Workup

  1. customconsumed
  2. temperaturethe mixture was heated to 70° C. for 30 min
  3. customThe mixture was purified by column chromatography (eluting with 30˜50% methanol in dichloromethane)

Sources & evidence

ORD record
ord-bd705185a78141db9ec33d30db5c06ac
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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