Sodium borohydride → HCID 86611601, compound

HRID 1350164Notes

Reaction equation

HRID 1350164 reaction equation
[CH:1]([O:4][C:5]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]2[C:11]3[O:19][C@H:20]4[CH2:25][CH2:24][CH2:23][C@H:21]4[NH:22][C:10]=3[CH:9]=[CH:8][C:7]=2[N:6]=1)([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)(C(F)(F)F)=O>[CH:1]([O:4][C:5]1[CH:14]=[C:13]([C:15]([F:17])([F:16])[F:18])[C:12]2[C:11]3[O:19][C@H:20]4[CH2:25][CH2:24][CH2:23][C@H:21]4[N:22]([CH2:13][C:15]([F:18])([F:17])[F:16])[C:10]=3[CH:9]=[CH:8][C:7]=2[N:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69318814HCID 69318814, compound

Product 1

HCID 86611601HCID 86611601, compoundYield 161.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 135 was prepared according to General Method 6 (EXAMPLE 3) from (7aR,10aS)-7,7a,8,9,10,10a-hexahydro-3-isopropoxy-1-(trifluoromethyl)-cyclopenta[5,6][1,4]oxazino[2,3-f]quinoline (20 mg, 0.057 mmol) and NaBH4 pellets (excess) in 7 mL TFA to afford 20 mg of (7aR,10aS)-7,7a,8,9,10,10a-hexahydro-3-isopropoxy-1-(trifluoromethyl)-7-(2,2,2-trifluoroethyl)-cyclopenta[5,6][1,4]oxazino[2,3-f]quinoline. This material (20 mg, 0.046 mmol) was carried on according to General Method 4 (EXAMPLE 1) by treatment with 6 mL of 1:1 acetic acid:concentrated HCl (0.01 M) heated at 90° C. for 4 h to afford 15 mg (83%) of Compound 135, a yellow solid, after column chromatography (3:1 hexanes:EtOAc to 1:1 hexanes:EtOAc, gradient elution). 1H NMR (500 MHz, CDCl3) δ12.10 (bs, 1H), 7.15 (s, 1H), 7.10 (d, J=8.8, 1H), 7.01 (d, J=8.8, 1H), 4.14 (m, 1H), 3.94 (m, 2H), 3.72 (ddd, J=10.5, 7.6, 3.4, 1H), 2.18 (m, 2H), 2.01 (m, 2H), 1.68 (m, 2H).

Sources & evidence

ORD record
ord-b75dd89670a3416392bf0433f490d0f8
Source dataset
uspto-grants-2007_05
Patent number
US07214690B2

Reaction notes

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