tert-Butanol → (3R,4R)-1-Benzyloxycarbonyl-3-(1-tert-butoxycarbonylaminocyclopropyl)-4-methylpyrrolidine

HRID 635069Notes

Reaction equation

HRID 635069 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([CH3:16])[C@@H:13]([C:17]2(C(O)=O)[CH2:19][CH2:18]2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.C([N:42]([CH2:45]C)CC)C.[C:47]([OH:51])([CH3:50])([CH3:49])[CH3:48]>>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([CH3:16])[C@@H:13]([C:17]2([NH:42][C:45]([O:51][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:30])[CH2:18][CH2:19]2)[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 695653671-[(3S,4R)-1-Benzyloxycarbonyl-4-methyl-3-Pyrrolidinyl]cyclopropanecarboxylic acid

Product 1

HCID 54433189(3R,4R)-1-Benzyloxycarbonyl-3-(1-tert-butoxycarbonylaminocyclopropyl)-4-methylpyrrolidineYield 58%

Procedure

1-[(3S,4R)-1-Benzyloxycarbonyl-4-methyl-3-pyrrolidinyl]cyclopropanecarboxylic acid (1.20 g, 3.66 mmol) was dissolved in tert-butyl alcohol (50 ml), and the solution was mixed with diphenylphosphoryl azide (0.946 ml, 4.39 mmol) and triethylamine (1.02 ml, 7.32 mmol) and heated under reflux for 19 hours. After completing the reaction, the solvent was evaporated and the resulting residue was purified by silica gel column chromatography (silica gel, 120 ml; ethyl acetate:hexane=1:2), to thereby obtain 0.793 g (58%) of the title compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 19 hours
  3. customthe reaction
  4. customthe solvent was evaporated
  5. customthe resulting residue was purified by silica gel column chromatography (silica gel, 120 ml; ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-7cebe9cc29d347769e6259962da7fb29
Source dataset
uspto-grants-2001_02
Patent number
US06184388B2

Reaction notes

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