Dimethyl Sulfide → HCID 8259841, compound

HRID 75143Notes

Reaction equation

HRID 75143 reaction equation
[C:1]12([CH2:11][NH:12][C:13](=O)[C@@H:14]([OH:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.S(C)C>C1COCC1>[C:1]12([CH2:11][NH:12][CH2:13][C@H:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[OH:21])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 59437171(S)-N-((1-adamantyl)methyl)-2-hydroxy-2-phenylacetamide

Product 1

HCID 8259841HCID 8259841, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)—N-((1-adamantyl)methyl)-2-hydroxy-2-phenylacetamide (85 mg, 0.28 mmol) in THF (10 mL) was added BH3.Me2S (10 M, 85 μL, 8.5 mmol) under nitrogen. The mixture was heated under reflux overnight and then cooled to rt. The reaction was quenched with methanol. The mixture was concentrated in vacuum to give crude product, which was purified by preparative TLC to afford (S)-2-((1-adamantylmethyl)amino)-1-phenylethanol (40 mg, 50%). 1H NMR (MeOD, 400 MHZ): δ=1.31-2.01 (m, 15H), 2.42 (q, 2H), 2.81 (d, 2H), 4.88 (t, 1H), 7.21-7.43(m, 5H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. customThe reaction was quenched with methanol
  4. concentrationThe mixture was concentrated in vacuum
  5. customto give crude product, which
  6. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-d6763e10c7eb4828b71a57eb2f7fb259
Source dataset
uspto-grants-2014_09
Patent number
US08835426B2

Reaction notes

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