Benzene → (3R,6R,7aS)-4-(6-Benzyloxy-3-tert-butyl-1-oxo-tetrahydro-pyrrolo[1,2-c]imidazol-2-yl)-naphthalene-1-carbonitrile

HRID 434078Notes

Reaction equation

HRID 434078 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([NH:13][C:14]([C@@H:16]2[CH2:20][C@@H:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:18][NH:17]2)=[O:15])=[CH:5][CH:4]=1)#[N:2].[CH:29](=O)[C:30]([CH3:33])([CH3:32])[CH3:31].C1C=CC=CC=1>CCCCC>[CH2:22]([O:21][C@H:19]1[CH2:18][N:17]2[C@@H:29]([C:30]([CH3:33])([CH3:32])[CH3:31])[N:13]([C:6]3[C:7]4[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[C:14](=[O:15])[C@@H:16]2[CH2:20]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 12417PivalaldehydeHCID 58583621(2S,4R)-4-Benzyloxy-pyrrolidine-2-carboxylic acid (4-cyano-naphthalen-1-yl)-amide

Product 1

HCID 58583623(3R,6R,7aS)-4-(6-Benzyloxy-3-tert-butyl-1-oxo-tetrahydro-pyrrolo[1,2-c]imidazol-2-yl)-naphthalene-1-carbonitrileYield 86.3%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

A suspension of 33B (151 mg, 0.38 mmol) and pivalaldehyde (100 μl, 0.90 mmol) in a mixture of dry benzene (0.5 ml) and dry pentane (5.0 ml) was refluxed for 25 hr with a Dean-Starke receiver (Ref: Org. Lett., 2 (18) 2781-2783, (2000)). The reaction mixture was evaporated to dryness and dried in vacuo. Purification using automated flash chromatography (35 g silica gel column, EtOAc/hexane gradient) gave the title compound as a light pink-colored solid (144.1 mg, 86.3%). m.p. 155-157° C. MS (ES): m/z 440 [M+1]+.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customdried in vacuo
  3. customPurification

Sources & evidence

ORD record
ord-eaf70428297a4357838dd3dd6f78b427
Source dataset
uspto-grants-2003_12
Patent number
US06670386B2

Reaction notes

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