Dimethyl Sulfoxide → (S)-2-[(1R,4aR,5S,8aR)-5-(tert-butyldimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propionaldehyde

HRID 1858997Notes

Reaction equation

HRID 1858997 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([Si:15]([CH3:33])([CH3:32])[O:16][C@H:17]1[CH2:26][CH2:25][CH2:24][C@@:23]2([CH3:27])[C@H:18]1[CH2:19][CH2:20][CH2:21][C@@H:22]2[C@H:28]([CH3:31])[CH2:29][OH:30])([CH3:14])([CH3:13])[CH3:12].CCN(CC)CC>C(Cl)Cl>[C:11]([Si:15]([CH3:33])([CH3:32])[O:16][C@H:17]1[CH2:26][CH2:25][CH2:24][C@@:23]2([CH3:27])[C@H:18]1[CH2:19][CH2:20][CH2:21][C@@H:22]2[C@H:28]([CH3:31])[CH:29]=[O:30])([CH3:13])([CH3:14])[CH3:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 21309368(S)-2-[(1R,4aR,5S,8aR)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propan-1-ol

Product 1

HCID 57255936(S)-2-[(1R,4aR,5S,8aR)-5-(tert-butyldimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propionaldehydeYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Swern reagent was prepared at -60° C. by adding slowly DMSO (0.899 ml, 11.5 mmol, dissolved in 2 ml of CH2Cl2) to oxalylchloride (0.503 ml, 5.85 mmol) in 10 ml of CH2Cl2. 15 Minutes later, (S)-2-[(1R,4aR,5S,8aR)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propan-1-ol (1.81 g, 5.31 mmol), dissolved in 7 ml of CH2Cl2, was slowly added. After 1/2 h, NEt3 (5.18 ml, 37.2 mmol) was added and the temperature allowed to reach -25° C. The reaction was quenched by pouring onto crashed ice/NH4Cl, extracted twice with ether, washed with water and brine, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=97/3) yielded 1.583 g of (S)-2-[(1R,4aR,5S,8aR)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propionaldehyde as isomerically pure, colorless oil.

Workup

  1. additionwas slowly added
  2. customto reach -25° C
  3. customThe reaction was quenched
  4. additionby pouring
  5. extractionextracted twice with ether
  6. washwashed with water and brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-679dac1037e2482d911879ab0fe1b034
Source dataset
uspto-grants-2000_11
Patent number
US06153605

Reaction notes

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