Sodium Hydroxide → HCID 14270694, compound

HRID 929540Notes

Reaction equation

HRID 929540 reaction equation
C([C@H]1COC(=O)N1[C:14](=[O:25])[C@H:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24])[CH3:16])C1C=CC=CC=1.[Li+].[BH4-].[OH-].[Na+].COC1C=CC=CC=1[C@H](C)CNC1C=C(C2C=NC(N3CCN(C)CC3)=CC=2)N=CN=1>C1COCC1.CO>[CH3:24][O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C@H:15]([CH3:16])[CH2:14][OH:25]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 73214428HCID 73214428, compoundHCID 86699653HCID 86699653, compound

Product 1

HCID 14270694HCID 14270694, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

As shown in step 5-iii of Scheme 5, to an ice-cooled solution of (4S)-4-benzyl-3-[(2S)-2-(2-methoxyphenyl)-propanoyl]oxazolidin-2-one (3.10 g, 9.13 mmol) in THF (183 mL) and MeOH (1.24 mL) was added LiBH4 (9.13 mL of 2.0 M solution, 18.3 mmol) and the reaction was stirred at 0° C. for 2 hours, then warmed to room temperature over 18 hours. A solution of NaOH (18.6 mL of 2.0 M solution) was added and the reaction stirred until both layers were clear. The layers were separated and the aqueous layer was extracted with Et2O (2×). The organic extracts were combined and washed with H2O, brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography on silica gel (0 to 20% EtOAc in hexanes) to give (2S)-2-(2-methoxyphenyl)propan-1-ol (Compound 2016, 1.49 g, 95.4% yield) as a clear, colorless liquid: 1H NMR (300 MHz, CDCl3) δ 7.30-7.19 (m, 2H), 6.98 (td, J=7.5, 1.0 Hz, 1H), 6.95-6.86 (m, 1H), 3.85 (s, 3H), 3.83-3.63 (m, 2H), 3.56-3.38 (m, 1H), 1.84 (s, 1H), 1.30 (d, J=7.1 Hz, 3H); [α]D25.7+4.18 (c 1.11, CHCl3). This optical rotation compares with the rotation for Compound 2016 as described by Denmark S E et al. in J. Am. Chem. Soc. Vol. 132, pages 3612-3620 (2010) and by Matsumoto T et al., in Bull. Chem. Soc. Jpn. Vol. 58, 340-345 (1985).

Workup

  1. temperaturewarmed to room temperature over 18 hours
  2. stirringthe reaction stirred until both layers
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with Et2O (2×)
  5. washwashed with H2O, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography on silica gel (0 to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c405cbb5a78d4b5cb5e8a32814f0615a
Source dataset
uspto-grants-2016_03
Patent number
US09296701B2

Reaction notes

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