4-Nitrobenzoic Acid → cis-2-(Tert-butoxycarbonyl)amino-1-(4-nitrobenzoyloxy)cyclopentane

HRID 1912723Notes

Reaction equation

HRID 1912723 reaction equation
[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])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:34]([C:37]1[CH:45]=[CH:44][C:40]([C:41](O)=[O:42])=[CH:39][CH:38]=1)([O-:36])=[O:35].N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[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:41](=[O:42])[C:40]1[CH:39]=[CH:38][C:37]([N+:34]([O-:36])=[O:35])=[CH:45][CH:44]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 45091953(1R,2R)-trans-N-Boc-2-Aminocyclopentanol

Product 1

HCID 69133449cis-2-(Tert-butoxycarbonyl)amino-1-(4-nitrobenzoyloxy)cyclopentaneYield 70.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-2-(tert-butoxycarbonyl)aminocyclopentan-1-ol (Prepn. 47, 3.00 g) triphenyl phosphine (5.90 g) and 4-nitrobenzoic acid (2.50 g) in THF (90 mL) was added, at 0° C., diisopropyl azodicarboxylate (4.50 mL). After stirring for 4 h, the solvent was evaporated and the crude product was purified by flash chromatography (SiO2, CH2Cl2:acetone 99:1) to give cis-2-(tert-butoxycarbonyl)amino-1-(4-nitrobenzoyloxy)cyclopentane (3.70 g, 70%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 8.33 (2H, d), 8.23 (2H, d), 7.08 (1H, d), 5.25 (1H, m), 3.92 (1H, m), 1.40-2.10 (6H, m), 1.28 (9H, s).

Workup

  1. customthe solvent was evaporated
  2. customthe crude product was purified by flash chromatography (SiO2, CH2Cl2:acetone 99:1)

Sources & evidence

ORD record
ord-3a2be80130c247af856ed778220502ee
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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