Ethanolamine → HCID 67005971, compound

HRID 564357Notes

Reaction equation

HRID 564357 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C@@H:9]2[C:18]3[C:13](=[C:14]([F:20])[CH:15]=[CH:16][C:17]=3[F:19])[O:12][CH2:11][C@H:10]2[CH:21]=O)=[CH:4][CH:3]=1.[CH2:23]([CH2:25][NH2:26])[OH:24].[BH4-].[Na+].CO>C1COCC1.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH:9]2[C:18]3[C:13](=[C:14]([F:20])[CH:15]=[CH:16][C:17]=3[F:19])[O:12][CH2:11][CH:10]2[CH2:21][NH:26][CH2:25][CH2:23][OH:24])=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 700EthanolamineHCID 887MethanolHCID 4311764Sodium borohydrideHCID 58445381rel-(3R,4R)-4-[(4-Chlorophenyl)thio]-5,8-difluoro-3,4-dihydro-2H-1-benzopyran-3-carboxaldehyde

Product 1

HCID 67005971HCID 67005971, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trans-4-(4-chloro-phenylsulfanyl)-5,8-difluoro-chroman-3-carbaldehyde (2.2 g, 5.9 mmole) and ethanolamine (1.1 g, 18 mmole) were dissolved in 20 ml THF. The reaction was stirred at room temperature overnight. 2 g Sodium borohydride and 10 ml MeOH were added and the reaction was stirred for three hours. 100 ml water and 100 ml EtOAc were added. The organic layer washed with water, dried over sodium sulfate and concentrated. The product was purified by column chromatography (EtOAc/hexane from 25/75 to 100/0 in 45 minutes). Yield, 0.40 g, 17.5%. 1H NMR (CDCl3 400 MHz) δ 7.45 (d, J=8.1 Hz, 2H), 7.31 (d, J=8.1 Hz, 2H), 6.92-7.00 (m, 1H), 6.54-6.60 (m, 1H), 4.62 (dd, J=8.8 and 2.2 Hz, 1H), 4.48 (br, 1H), 4.38 (dt, J=11.7 and 2.2 Hz, 1H), 3.55 (t, J=5.1 Hz, 2H), 2.67 (dd, J=12.4 and 7.3 Hz, 1H), 2.62 (t, J=5.1 Hz, 2H), 2.48 (dd, J=12.4 and 8.1 Hz, 1H), 2.09 (m, 1H).

Workup

  1. stirringthe reaction was stirred for three hours
  2. washThe organic layer washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe product was purified by column chromatography (EtOAc/hexane from 25/75 to 100/0 in 45 minutes)
  6. customYield

Sources & evidence

ORD record
ord-e99e2149e1784170be19668e4ef69272
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

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