Hydrochloric Acid → 1-Tert-butyl 3-methyl 4-hydroxypiperidine-1,3-dicarboxylate

HRID 1842053Notes

Reaction equation

HRID 1842053 reaction equation
C(N(CC)CC)C.[O:8]=[C:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH:10]1[C:22]([O:24][CH3:25])=[O:23].[BH4-].[Na+].Cl>CO>[OH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:11][CH:10]1[C:22]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 112768931-tert-Butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate

Product 1

HCID 185348061-Tert-butyl 3-methyl 4-hydroxypiperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a flask, methanol (1.425 mL) and triethylamine (0.0277 g, 0.274 mmol) was added to 1-tert-butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate (0.0587 g, 0.228 mmol). The reaction was allowed to stir at room temperature for 15 minutes. Sodium borohydride (0.0285 g, 0.753 mmol) was added to the flask one portion. The reaction was allowed to stir at room temperature for an additional hour. Using 1N hydrochloric acid, the reaction was neutralized to pH 7 and then concentrated under vacuo. Water (2 mL) was used to dissolve the residue. The mixture was extracted using dichloromethane (3×2 mL). The extracts were combined, washed with saturated sodium bicarbonate, dried using sodium sulfate, and concentrated under vacuo. The crude product was progressed to the next step without further purification.

Workup

  1. stirringto stir at room temperature for an additional hour
  2. concentrationconcentrated under vacuo
  3. dissolutionto dissolve the residue
  4. extractionThe mixture was extracted
  5. washwashed with saturated sodium bicarbonate
  6. customdried
  7. concentrationconcentrated under vacuo
  8. customThe crude product was progressed to the next step without further purification

Sources & evidence

ORD record
ord-c348bc38b8ac430cac928dbdc48b168c
Source dataset
uspto-grants-2015_02
Patent number
US08946216B2

Reaction notes

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