Acetic Acid → HCID 69321594, compound

HRID 1350163Notes

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:28](O)(=O)[CH3:29]>>[CH2:28]([N:22]1[C:10]2[CH:9]=[CH:8][C:7]3[N:6]=[C:5]([O:4][CH:1]([CH3:3])[CH3:2])[CH:14]=[C:13]([C:15]([F:17])([F:16])[F:18])[C:12]=3[C:11]=2[O:19][C@H:20]2[CH2:25][CH2:24][CH2:23][C@@H:21]12)[CH3:29]

Participants

Reactant 3

HCID 176Acetic Acid

HCID 4311764Sodium borohydride

HCID 69318814HCID 69318814, compound

Product 1

HCID 69321594HCID 69321594, compound

Procedure

Compound 134 was prepared according to General Method 5 (EXAMPLE 2) from (7aR,10aS)-7,7a,8,9,10,10a-hexahydro-3-isopropoxy-1-(trifluoromethyl)-cyclopenta[5,6][1,4]oxazino[2,3-f]quinoline (5 mg, 0.014 mmol) and NaBH4 pellets (>10 equiv) in 5 mL acetic acid to afford 5 mg of (7aR,10aS)-7-ethyl-7,7a,8,9,10,10a-hexahydro-3-isopropoxy-1-(trifluoromethyl)-cyclopenta[5,6][1,4]oxazino[2,3-f]quinoline. This material (5 mg, 0.01 mmol) was carried on according to General Method 4 (EXAMPLE 1) by treatment with 4 mL of 1:1 acetic acid:concentrated HCl (3 mM) and heated at 90° C. for 4 h to afford 4 mg (89%) of Compound 134, a yellow solid, after column chromatography (3:1 hexanes:EtOAc to 1:1 hexanes:EtOAc, gradient elution). 1H NMR (500 MHz, CDCl3)δ11.01 (bs, 1H), 7.10 (s, 1H), 7.01 (d, J=8.8, 1H), 6.90 (d, J=8.8, 1H), 4.00 (m, 1H), 3.59 (ddd, J=10.0, 7.1, 3.4 1H), 3.44 (m, 2H), 2.03 (m, 4H), 1.61 (m, 2H), 1.20 (t, J=7.1, 3H).

Sources & evidence

ORD record: ord-ca16a41a3b9e470d939a4bbf84a0c849
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214690B2

Reaction notes

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