Ammonia → HCID 22870381, compound

HRID 975700Notes

Reaction equation

HRID 975700 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][C@H:8]1[CH2:32][CH2:33][N:34]=[N+]=[N-])=[O:6])[CH:2]=[CH2:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N>N1C=CC=CC=1>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][C@H:8]1[CH2:32][CH2:33][NH2:34])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 11776TriphenylphosphineHCID 57296959HCID 57296959, compound

Product 1

HCID 22870381HCID 22870381, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (2R,4S)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-(triphenylmethylthio) pyrrolidine (10.1 g) in pyridine (30 ml) was added triphenylphosphine at ambient temperature. The mixture was stirred at the same temperature for 1 hour, and then 28% aqueous ammonia was added. After stirring at ambient temperature overnight, the mixture was evaporated under reduced pressure, and co-evaporated with toluene. The residue was column chromatographed on silica gel (chloroform:methanol=9:1) to give (2R,4S)-1-allyloxycarbonyl-2-(2-aminoethyl)-4(triphenylmethylthio)pyrrolidine (9.0 g).

Workup

  1. stirringAfter stirring at ambient temperature overnight
  2. customthe mixture was evaporated under reduced pressure
  3. customchromatographed on silica gel (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-77d883f0c6ac44cdbb8f04c6410a944f
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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