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1,8-Diazabicyclo(5.4.0)undec-7-ene → (+/-)-(3aR*,8aS*)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo-[2,3-b]indol-4-yl (R)-(alpha-methylbenzyl)carbamate

HRID 1770
Notes
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Reaction equation

HRID 1770 reaction equation
[CH3:1][N:2]1[C@@H:6]2[N:7]([CH3:15])[C:8]3[CH:9]=[CH:10][CH:11]=[C:12]([OH:14])[C:13]=3[C@:5]2([CH3:16])[CH2:4][CH2:3]1.C1CCN2C(=NCCC2)CC1.[CH3:28][CH:29]([N:36]=[C:37]=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1>[CH3:28][C@@H:29]([NH:36][C:37](=[O:38])[O:14][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:13]=1[C@@:5]1([CH3:16])[CH2:4][CH2:3][N:2]([CH3:1])[C@H:6]1[N:7]2[CH3:15])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 85760alpha-Methylbenzyl isocyanateHCID 88402553cis-(+/-)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo [2,3-b]indol-4-ol

Product 1

HCID 53984692(+/-)-(3aR*,8aS*)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo-[2,3-b]indol-4-yl (R)-(alpha-methylbenzyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

cis-(±)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo [2,3-b]indol-4-ol (2g) was dissolved in degassed THF (200 ml). DBU (0.8 ml) was added to the mixture followed by R-(+)-α-methylbenzyl isocyanate (2 g). The reaction was stirred at room temperature overnight under nitrogen. The solvent was evaporated under reduced pressure and the residue was purified using Prep 500 chromatography (4% MeOH/DCM) to yield 1.2 g of a solid. This material was combined with 600 mg of identically prepared material, which was found to be pure by thin layer analysis. The combined product was triturated with isopropyl ether and filtered to yield 1.8 g of (±)-(3aR*, 8aS*)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo [2,3-b]indol-4-yl (R)-(α-methylbenzyl)carbamate, m.p. 151°-155° C.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified

Sources & evidence

ORD record
ord-cb9d1bc99b9b4ab18c65744a87225d92
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05726323

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes