Dimethyl Sulfide → HCID 54202943, compound

HRID 1386689Notes

Reaction equation

HRID 1386689 reaction equation
B1(C)[O:8][C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@@H]2N1CCC2.B.CSC>C1(C)C=CC=CC=1.C(Cl)Cl.C1COCC1>[CH:20]1([CH2:15][C@@H:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[OH:8])[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 3

HCID 1068Dimethyl SulfideHCID 6331BoraneHCID 9838490(R)-2-Methyl-CBS-oxazaborolidine

Product 1

HCID 54202943HCID 54202943, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.7 mL of 1.0 M (R)-2-methyl-CBS-oxazaborolidine solution in toluene in 4 mL of CH2Cl2 at −25° C. was treated with 1.4 mL of 2.0 M borane.methyl sulfide in THF and stirred cold for 10 min. A solution of 501 mg (2.66 mmol) of cyclopentylmethylene phenyl ketone (from EXAMPLE 20, Step B) in 2 mL of CH2Cl2 was added over 25 min and the resulting mixture was stirred cold for 45 min. The reaction was quenched by pouring it into cold (−25° C.) MeOH. The quenched reaction was warmed to rt and stirred for 45 min until gas evolution ceased. The mixture was concentrated and the residue dissolved in 20 mL of MeOH and concentrated again. Flash chromatography on silica gel using 17:3 v/v hexanes/EtOAc afforded 413 mg (81%) of the title compound: RF: 0.53 (4:1 v/v hexanes/EtOAc); 1H NMR (300 MHz) δ 1.10-1.17 (m, 2H), 1.47-1.89 (m, 9H), 4.69 (m, 1H), 7.25-7.35 (m, 5H).

Workup

  1. customThe reaction was quenched
  2. additionby pouring it into cold (−25° C.) MeOH
  3. customThe quenched reaction
  4. stirringstirred for 45 min until gas evolution
  5. concentrationThe mixture was concentrated
  6. dissolutionthe residue dissolved in 20 mL of MeOH
  7. concentrationconcentrated again

Sources & evidence

ORD record
ord-747749f126fd4facb8541d8f453a8f2a
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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