Acetic Acid → HCID 67071489, compound

HRID 874274Notes

Reaction equation

HRID 874274 reaction equation
[CH3:1][O:2][C:3](=[O:30])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:26](=[CH:27][CH:28]=1)[O:25][C:11]1([CH2:17][CH2:16][CH2:15][N:14]([C:18](OC(C)(C)C)=O)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:29].CC(O)=O.[F:35][C:36]1[CH:43]=[CH:42][C:39](C=O)=[CH:38][CH:37]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:30])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:26](=[CH:27][CH:28]=1)[O:25][C:11]1([CH2:17][CH2:16][CH2:15][N:14]([CH2:18][C:39]3[CH:42]=[CH:43][C:36]([F:35])=[CH:37][CH:38]=3)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:29]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 680234-FluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67071624HCID 67071624, compound2×

Product 1

HCID 67071489HCID 67071489, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(±)-(E)-3-[4-Oxo-spiro(chromane-2,4′-azepane)-6-yl]-acrylic acid methyl ester hydrochloride (Intermediate 3, 650 mg, 1.85 mmol) was suspended in DCM (100 ml). TEA (0.258 ml, 1.85 mmol) was added and the pH was adjusted to 5 with AcOH. 4-Fluorobenzaldehyde (275 mg, 2.22 mmol) and NaBH(OAc)3 (587 mg, 2.77 mmol) were added and the mixture was stirred for 6 h at RT, then washed with a saturated NaHCO3 solution brine, dried over Na2SO4 and evaporated to dryness. The crude mixture was purified by column chromatography (eluent DCM/MeOH 99:1) to give (±)-(E)-3-[1′(4-fluoro-benzyl)-4-oxo-spiro(chromane-2,4′-azepane)-6-yl]-acrylic acid methyl ester (550 mg)

Workup

  1. washwashed with a saturated NaHCO3 solution brine
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness
  4. customThe crude mixture was purified by column chromatography (eluent DCM/MeOH 99:1)

Sources & evidence

ORD record
ord-ad6ea7773c2d468a958cfb2cbceecbdf
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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