(4S,10aS)-4-aminohexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one → (4S,7R,10aS)-4-Amino-7-methylhexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one

HRID 529552Notes

Reaction equation

HRID 529552 reaction equation
[NH2:1][C@H:2]1[CH2:8][CH2:7][S:6][C@H:5]2[CH2:9][CH2:10][CH2:11][CH2:12][N:4]2[C:3]1=[O:13].F[C:15](F)(F)C(O)=O.N[C@H](C)CCCCO>>[NH2:1][C@H:2]1[CH2:8][CH2:7][S:6][C@H:5]2[CH2:9][CH2:10][CH2:11][C@@H:12]([CH3:15])[N:4]2[C:3]1=[O:13]

Participants

3

Reactant 2

HCID 86706213(4S,10aS)-4-aminohexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-oneHCID 86706229(R)-5-aminohexan-1-ol trifluoroacetate

Product 1

HCID 60127973(4S,7R,10aS)-4-Amino-7-methylhexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one

Procedure

(4S,7R,10aS)-4-Amino-7-methylhexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one (135 mg, 0.599 mmol) was synthesized as described for the preparation of Intermediate 40 using (R)-5-aminohexan-1-ol trifluoroacetate in step A. Anal. Calcd. for C10H18N2O5 m/z 214.3. found: 215.1 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 5.40-5.28 (m, 1H), 4.70-4.55 (m, 1H), 4.00 (ddd, J=14.7, 9.6, 5.2 Hz, 1H), 2.98-2.83 (m, 1H), 2.71-2.56 (m, 1H), 2.29-2.13 (m, 1H), 2.03-1.45 (m, 7H), 1.57-1.45 (m, 1H), 1.39-1.31 (m, 1H), 1.31 (d, J=7.0 Hz, 3H).

Sources & evidence

ORD record
ord-a176e3d1708c49349a680569f8d5b962
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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