Formic Acid → HCID 86744910, compound

HRID 1086801Notes

Reaction equation

HRID 1086801 reaction equation
N(C(OCC)=O)=N[C:3](OCC)=[O:4].[OH:13][C@@H:14]1[CH2:18][CH2:17][C@H:16]([NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:15]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)=O>C1COCC1.CCOCC.C1CCCCC1>[CH:3]([O:13][C@H:14]1[CH2:18][CH2:17][C@H:16]([NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:15]1)=[O:4]

Participants

8

Reactant 4

HCID 284Formic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86331931HCID 86331931, compound

Product 1

HCID 86744910HCID 86744910, compoundYield 88.6%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Procedure

Diethyl azodicarboxylate (1.78 g) was added dropwise to a stirred solution of N-(cis-3-hydroxycyclopentyl)carbamic acid, (phenylmethyl) ester (1.19 g), triphenylphosphine (2.68 g) and formic acid (0.47 g) in THF (65 ml) under nitrogen at room temperature. The resulting solution was stirred for 2 h, and concentrated to give a residue which was stirred in ether (20 ml) at ca -10° under nitrogen for 1 h. The mixture was diluted with cyclohexane (20 ml), and the solid was filtered off and washed with ether:cyclohexane (1:1; 3×ca. 20 ml). The combined filtrate and washings were concentrated, and the resultant residue was purified by FCC eluting with ethyl acetate:cyclohexane (2:3) to give the title compound (1.18 g), m.p. 45°-48°.

Workup

  1. concentrationconcentrated
  2. customto give a residue which
  3. filtrationthe solid was filtered off
  4. washwashed with ether:cyclohexane (1:1; 3×ca. 20 ml)
  5. concentrationThe combined filtrate and washings were concentrated
  6. customthe resultant residue was purified by FCC
  7. washeluting with ethyl acetate:cyclohexane (2:3)

Sources & evidence

ORD record
ord-ab8f1073898b4d2f92c175e127286fac
Source dataset
uspto-grants-1991_07
Patent number
US05032583

Reaction notes

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