Triphenylphosphine → HCID 21345250, compound

HRID 2185747Notes

Reaction equation

HRID 2185747 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+]>C1COCC1.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

8

Reactant 5

HCID 11776TriphenylphosphineHCID 14797Potassium HydroxideHCID 5462977Diethyl azodicarboxylateHCID 10511797tert-butyl (2S)-2-(hydroxymethyl)azetidine-1-carboxylateHCID 13250412(5-Hydroxypyridin-2-yl)methyl acetate

Product 1

HCID 21345250HCID 21345250, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

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 THF (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-4122fd3a268441ad8394b1e1259b820f
Source dataset
uspto-grants-2002_06
Patent number
US06403575B1

Reaction notes

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