Allylamine → HCID 10733764, compound

HRID 2186542Notes

Reaction equation

HRID 2186542 reaction equation
Cl.[CH2:2]([O:4][C:5]([C:7]1[CH2:12][C@H:11](OS(C)(=O)=O)[C@@H:10]([NH2:18])[C@H:9]([O:19][CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH:8]=1)=[O:6])[CH3:3].[CH2:25]([NH2:28])[CH:26]=[CH2:27]>>[CH2:2]([O:4][C:5]([C:7]1[CH2:12][C@H:11]([NH:28][CH2:25][CH:26]=[CH2:27])[C@@H:10]([NH2:18])[C@H:9]([O:19][CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH:8]=1)=[O:6])[CH3:3]

Participants

3

Reactant 2

HCID 7853AllylamineHCID 86584169HCID 86584169, compound

Product 1

HCID 10733764HCID 10733764, compoundYield 316.8%

Conditions

Temperature
110 °C

Procedure

A solution of 6.95 g (19.9 mmol) of (3R,4S,5S)-4-amino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester hydrochloride and 6.1 ml (79. 6 mmol) of allylamine in 82 ml of tert.-butyl methyl ester was sealed in a pressure vessel under argon and heated to 110° C., resulting in a 4 bar internal pressure. After 20 h the mixture was cooled to room temperature and partitioned between 30 ml of tert.-butyl methyl ester and 120 ml of saturated sodium bicarbonate solution. The aqueous phase was extracted with 50 ml tert.-butyl methyl ester, and the combined organic phases were dried over sodium sulfate, filtered and evaporated to give 5.90 g (96%) of product as a slightly brownish oil. Purity: 77% (ISTD).

Workup

  1. customresulting in a 4 bar internal pressure
  2. temperatureAfter 20 h the mixture was cooled to room temperature
  3. custompartitioned between 30 ml of tert.-butyl methyl ester and 120 ml of saturated sodium bicarbonate solution
  4. extractionThe aqueous phase was extracted with 50 ml tert.-butyl methyl ester
  5. dry with materialthe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-85cdf88b33444306b859446db533ccf1
Source dataset
uspto-grants-2002_06
Patent number
US06403824B2

Reaction notes

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