4H-Thieno[3,2-e]-1,2-thiazin-4-one, 6-chloro-2,3-dihydro-2-(3-methoxypropyl)-, 1,1-dioxide → (4S)-6-chloro-2-(3-methoxypropyl)-1,1-dioxo-3,4-dihydrothieno(3,2-e)thiazin-4-ol

HRID 129927Notes

Reaction equation

HRID 129927 reaction equation
[Cl:1][C:2]1[S:10][C:9]2[S:8](=[O:12])(=[O:11])[N:7]([CH2:13][CH2:14][CH2:15][O:16][CH3:17])[CH2:6][C:5](=[O:18])[C:4]=2[CH:3]=1>C1(B2N3CCC[C@H]3C(C3C=CC=CC=3)(C3C=CC=CC=3)O2)C=CC=CC=1>[Cl:1][C:2]1[S:10][C:9]2[S:8](=[O:12])(=[O:11])[N:7]([CH2:13][CH2:14][CH2:15][O:16][CH3:17])[CH2:6][C@@H:5]([OH:18])[C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 108705954H-Thieno[3,2-e]-1,2-thiazin-4-one, 6-chloro-2,3-dihydro-2-(3-methoxypropyl)-, 1,1-dioxide

Product 1

HCID 9926764(4S)-6-chloro-2-(3-methoxypropyl)-1,1-dioxo-3,4-dihydrothieno(3,2-e)thiazin-4-ol

Reagents, catalysts & solvents 1

HCID 10903897(S)-1,3,3-Triphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaboroleCatalyst

Procedure

Starting with 9.3 g of ketone 6 and following the same procedure as mentioned in Example 5 except using a stock solution of 1M (S)-tetrahydro-1,3,3-triphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole as catalyst led to 1, 4.9 g (52%) yield, ee=65%.

Workup

  1. customyield

Sources & evidence

ORD record
ord-23f6553ec2864914a06d67add3947520
Source dataset
uspto-grants-1995_11
Patent number
US05470973

Reaction notes

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