Formic Acid → (1S,3S)-3-[(tert-Butoxycarbonyl)amino]cyclopentyl formate

HRID 582532Notes

Reaction equation

HRID 582532 reaction equation
N(C(OCC)=O)=N[C:3](OCC)=[O:4].[CH3:13][C:14]([O:17][C:18](=[O:26])[NH:19][C@H:20]1[CH2:24][CH2:23][C@@H:22]([OH:25])[CH2:21]1)([CH3:16])[CH3:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)=O>>[CH3:16][C:14]([O:17][C:18](=[O:26])[NH:19][C@H:20]1[CH2:24][CH2:23][C@H:22]([O:25][CH:3]=[O:4])[CH2:21]1)([CH3:13])[CH3:15]

Participants

5

Reactant 4

HCID 284Formic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 216370811,1-Dimethylethyl N-((1S,3R)-3-hydroxycyclopentyl)carbamate

Product 1

HCID 86754023(1S,3S)-3-[(tert-Butoxycarbonyl)amino]cyclopentyl formateYield 50.1%

Procedure

Diethyl azodicarboxylate (0.164 ml, 1.23 mmol) was added dropwise to a stirred solution of (1S-cis)-(3-hydroxycyclopentyl)carbamic acid 1,1-dimethylethyl ester (0.124 g, 0.61 mmol), triphenylphosphine (0.323 g, 1.23 mmol) and formic acid (0.046 ml, 1.23 mmol) and the solution was stirred at room temperature for 2h. The solution was then concentrated and purified by column chromatography on flash silica eluting with 10-30% ethyl acetate in cyclohexane to give the title compound (0.07 g) as white needles from diisopropyl ether m.p.84-85° C., [α]D -12.7° (CHCl3 c=0.55%).

Workup

  1. concentrationThe solution was then concentrated
  2. custompurified by column chromatography on flash silica eluting with 10-30% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-f79d2b6ba67a4756968baf3fe0b07dc3
Source dataset
uspto-grants-1999_07
Patent number
US05925624

Reaction notes

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