Ethanolamine → HCID 70871943, compound

HRID 1047522Notes

Reaction equation

HRID 1047522 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]([NH:26][CH2:25][CH2:23][OH:24])[CH:10]2[CH2:21][C:18]3[C:13](=[C:14]([F:20])[CH:15]=[CH:16][C:17]=3[F:19])[O:12][CH2:11]2)=[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 70871943HCID 70871943, 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 was 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 was 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-fa8445692ae441859e49f51d724a6f30
Source dataset
uspto-grants-2013_10
Patent number
US08569521B2

Reaction notes

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