Tetrabutylammonium Fluoride → 2-Oxazolidinone, 5-[(3-chlorophenoxy)methyl]-3-(2-hydroxy-1-methylethyl)-, [R-(R*,R*)]-

HRID 1901698Notes

Reaction equation

HRID 1901698 reaction equation
[Si]([O:8][CH2:9][C@H:10]([N:12]1[CH2:16][C@H:15]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[O:14][C:13]1=[O:26])[CH3:11])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:25][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[O:18][CH2:17][C@@H:15]1[O:14][C:13](=[O:26])[N:12]([C@H:10]([CH3:11])[CH2:9][OH:8])[CH2:16]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 53837598HCID 53837598, compound

Product 1

HCID 677415862-Oxazolidinone, 5-[(3-chlorophenoxy)methyl]-3-(2-hydroxy-1-methylethyl)-, [R-(R*,R*)]-Yield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A procedure similar to that described in Preparation 5(b) was repeated, except that 3.25 g of 3-[2-t-butyldimethylsilyloxy-1(R)-methylethyl]-5(R)-(3-chlorophenoxymethyl)oxazolidin-2-one (prepared as described in Preparation 43), 24 ml of tetrabutylammonium fluoride (26% w/v in tetrahydrofuran) and 30 ml of anhydrous tetrahydrofuran were used, to give 2.28 g of the title compound, melting at 76° C. to 78° C. and having [α]D =-65.4° (methanol, c=1.060).

Sources & evidence

ORD record
ord-7d6481ed970643c5913afc55d95ce389
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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