Potassium Carbonate → tert-butyl (1S,2R)-2-hydroxycyclopentylcarbamate

HRID 1912724Notes

Reaction equation

HRID 1912724 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[O:14]C(=O)C1C=CC([N+]([O-])=O)=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.O.C(=O)([O-])[O-].[K+].[K+]>O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[OH:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22242641Methanol--water (1/1)HCID 69133449cis-2-(Tert-butoxycarbonyl)amino-1-(4-nitrobenzoyloxy)cyclopentane

Product 1

HCID 51416200tert-butyl (1S,2R)-2-hydroxycyclopentylcarbamateYield 91.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of cis-2-(tert-butoxycarbonyl)amino-1-(4-nitrobenzoyloxy)cyclopentane (3.70 g) in a mixture methanol/water 1:1 (20 mL) at room temperature, potassium carbonate (2.37 g) was added and stirred overnight. Water was added and the mixture extracted with diethyl ether. The combined organic layers were separated, dried over Na2SO4 and evaporated to dryness to give cis-2-(tert-butoxycarbonyl)aminocyclopentan-1-ol (1.94 g, 91%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 6.09 (1H, d), 4.54 (1H, bb), 3.86 (1H, m), 3.53 (1H, m), 1.30-1.80 (6H, m), 1.37 (9H, s).

Workup

  1. extractionthe mixture extracted with diethyl ether
  2. customThe combined organic layers were separated
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-5999b702935248e6b95791ccef888817
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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