HCID 18453470, compound → tert-butyl N-((1R,3S)-3-(hydroxymethyl)cyclopentyl)carbamate

HRID 2179743Notes

Reaction equation

HRID 2179743 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][C@H:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:4]1>C(O)C>[OH:1][CH2:2][C@H:3]1[CH2:4][CH2:5][C@@H:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14])[CH2:7]1

Participants

3

Reactant 1

HCID 18453470HCID 18453470, compound

Product 1

HCID 11962831tert-butyl N-((1R,3S)-3-(hydroxymethyl)cyclopentyl)carbamateYield 74.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of tert-butyl (1S,4R)-4-(hydroxymethyl)cyclopent-2-enylcarbamate (step 1, about 10.0 g) in ethanol (150 ml) 10% palladium on carbon (about 1.0 g) was added and kept under hydrogen atmosphere. Reaction mass was stirred for about 16 hours. Completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered through high-flow bed and washed with ethanol. The filtrate was concentrated under reduced pressure to furnish the title compound (7.5 g) as a light yellow liquid. ES Mass: 215 [M+1] 216 (100%).

Workup

  1. customReaction mass
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered through high-flow bed
  4. washwashed with ethanol
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-58d6473357e444208241bf8eb4a24ce9
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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