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

HRID 1954589Notes

Reaction equation

HRID 1954589 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-977259c0989a43fa96e94a539044a151
Source dataset
uspto-grants-2000_09
Patent number
US06121285

Reaction notes

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