Triacetoxyperiodinane → 2-[(3R)-12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]acetaldehyde

HRID 1503951Notes

Reaction equation

HRID 1503951 reaction equation
[N:1]1([CH:7]2[CH2:12][CH2:11][CH:10]([O:13][C:14]3[C:25]4[C:24]5[C@@H:23]([CH2:26][CH2:27][OH:28])[CH2:22][CH2:21][C:20]=5[S:19][C:18]=4[N:17]=[CH:16][N:15]=3)[CH2:9][CH2:8]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[N:1]1([CH:7]2[CH2:8][CH2:9][CH:10]([O:13][C:14]3[C:25]4[C:24]5[C@@H:23]([CH2:26][CH:27]=[O:28])[CH2:22][CH2:21][C:20]=5[S:19][C:18]=4[N:17]=[CH:16][N:15]=3)[CH2:11][CH2:12]2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 681155022-[(3R)-12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]ethan-1-ol

Product 1

HCID 866951092-[(3R)-12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]acetaldehydeYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 50-mL round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was charged with a dichloromethane (15 mL) solution of 2-[(3R)-12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]ethan-1-ol (200 mg, 0.50 mmol, 1.00 equiv). Dess-Martin periodinane (318 mg, 0.75 mmol, 1.51 equiv) was added and the resulting mixture was stirred for 2 hr at 0° C. in a water/ice bath. After completion, the reaction was quenched with sodium bicarbonate (sat.) and extracted with 3×60 mL of EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column with ethyl acetate/petroleum ether (1:1) to afford the corresponding 2-[(3R)-12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]acetaldehyde (150 mg, 75%) as a colorless oil. MS (ES): m/z 402 [M+H]+.

Workup

  1. customA 50-mL round-bottom flask, purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customAfter completion, the reaction was quenched with sodium bicarbonate (sat.)
  4. extractionextracted with 3×60 mL of EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified on a silica gel column with ethyl acetate/petroleum ether (1:1)

Sources & evidence

ORD record
ord-5b89431d8a7842e7a8cce58950e2acc5
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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