Triphenylphosphine → HCID 21345250, compound

HRID 367080Notes

Reaction equation

HRID 367080 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][OH:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O:17][CH2:18][C:19]1[N:24]=[CH:23][C:22](O)=[CH:21][CH:20]=1)(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[OH-].[K+]>CO>[OH:17][CH2:18][C:19]1[N:24]=[CH:23][C:22]([O:13][CH2:12][C@@H:9]2[CH2:10][CH2:11][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:21][CH:20]=1

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 14797Potassium HydroxideHCID 5462977Diethyl azodicarboxylateHCID 10511797tert-butyl (2S)-2-(hydroxymethyl)azetidine-1-carboxylateHCID 1325041289098-99-7

Product 1

HCID 21345250HCID 21345250, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A sample of (S)-1-t-butoxycarbonyl-2-azetidinemethanol (1.64 g, 8.18 mmol) and 1.05 g (6.29 mmol) of 6-acetyloxymethyl-3-hydroxypyridine, prepared as described by Deady and Dayhe, Aust. J. Chem., 2565:36 (1983), were reacted with triphenylphosphine (540 mg, 2.06 mmol) and DEAD (0.33 mL, 2.06 mmol) in TBF (25 mL) according to the procedure of Example 2a. The product was stirred in methanol (4 mL) containing KOH (450 mg) at room temperature for 4 hours, then neutralized and concentrated. The residue was purified by chromatography (silica gel; 1:1 ether: hexane and ethyl acetate) to give title compound (240 mg, 41% for two steps). MS (DCI/NH3) m/e: 295 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 1.42 (s, 9H), 2.24-2.48 (m, 2H), 3.84-3.96 (m, 2H), 4.18 (dd, J=2.6, 11 Hz, 1H), 4.40 (m, 1H), 4.53 (m, 1H), 4.82 (s, 2H), 7.36 (d, J=8.5 Hz, 1H), 7.51 (m 1H), 8.31 (d, J=3.0 Hz, 1H).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by chromatography (silica gel; 1:1 ether: hexane and ethyl acetate)

Sources & evidence

ORD record
ord-e6c5d4c93ddf4f3abf463edce2c1fa9e
Source dataset
uspto-grants-2000_10
Patent number
US06133253

Reaction notes

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