2-Methylpropylenediamine → 1-Boc-3-hydroxypiperidine

HRID 1903235Notes

Reaction equation

HRID 1903235 reaction equation
[C:1](=[O:12])([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])OC(C)(C)C.[OH:13][CH:14]1[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]1.CC(C)(N)CN>O.C(O)(C)(C)C>[C:8]([O:7][C:1]([N:16]1[CH2:17][CH2:18][CH2:19][CH:14]([OH:13])[CH2:15]1)=[O:12])([CH3:9])([CH3:10])[CH3:11]

Participants

6

Reactant 3

HCID 131282-MethylpropylenediamineHCID 232933-HydroxypiperidineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 5456991-Boc-3-hydroxypiperidine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Procedure

Di-t-butyl carbonate (11.9 g.) was added to a solution of 3-hydroxypiperidine (5.0 g.) in water (10 ml.) and t-butanol (5 ml.) at ambient temperature, and the mixture was stirred for 16 hr. at ambient temperature. 1,1-Dimethylethylenediamine (1.5 ml.) was added and the mixture was stirred at ambient temperature for 1 hr. The solution was poured into water (150 ml.) and extracted with diethyl ether (3×50 ml.). The diethyl ether extract was washed successively with 1 M-hydrochloric acid (50 ml.), saturated sodium carbonate solution (50 ml.) and brine (50 ml.), and then dried (MgSO4). The solvent was evaporated to give 1-t-butoxycarbonyl-3-hydroxypiperidine, which was used without further purification.

Workup

  1. customat ambient temperature
  2. stirringthe mixture was stirred at ambient temperature for 1 hr
  3. extractionextracted with diethyl ether (3×50 ml.)
  4. extractionThe diethyl ether extract
  5. washwas washed successively with 1 M-hydrochloric acid (50 ml.), saturated sodium carbonate solution (50 ml.) and brine (50 ml.)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-0eeba75ce8fb4dd9a2a72ea8bc58f78b
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

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