tert-Butyl 3-oxo-2-phenylpiperidine-1-carboxylate → HCID 19379354, compound

HRID 2210705Notes

Reaction equation

HRID 2210705 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH:9]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O)(C)(C)C.[CH3:21][Mg]Br>O1CCCC1>[CH3:21][C:10]1([OH:14])[CH2:11][CH2:12][CH2:13][NH:8][CH:9]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 11414684tert-Butyl 3-oxo-2-phenylpiperidine-1-carboxylateHCID 178418573HCID 178418573, compound

Product 1

HCID 19379354HCID 19379354, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-t-butoxycarbonyl-2-phenyl-piperidin-3-one (0.57 g, Example 48a)in 5 ml anhydrous tetrahydrofuran at -78° C. was treated with methyl magnesium bromide (1.6 ml of 1.5M solution in toluene-THF). The reaction was partitioned between saturated ammonium chloride-diethyl ether, the organic phase dried and evaporated in vacuo. The residue was chromatographed using 20% ethyl acetate in hexane as eluant to give 1-t-butoxycarbonyl, 3-methyl-2-phenyl piperidin-3-ol as a crystalline solid, m.p.=95°-97° C.

Workup

  1. customat -78° C.
  2. customThe reaction was partitioned between saturated ammonium chloride-diethyl ether
  3. customthe organic phase dried
  4. customevaporated in vacuo
  5. customThe residue was chromatographed

Sources & evidence

ORD record
ord-ef5917e872314a859669994d23f119e2
Source dataset
uspto-grants-1995_10
Patent number
US05459270

Reaction notes

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