Triacetoxyperiodinane → HCID 59396019, compound

HRID 1094753Notes

Reaction equation

HRID 1094753 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:9][C@H:8]2[C@H:6]([CH2:7]2)[CH2:5][N:4]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].C([O-])(O)=O.[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C1CCCCC1.CCOC(C)=O>C(Cl)Cl>[CH:2]([C@@H:3]1[CH2:9][C@H:8]2[C@H:6]([CH2:7]2)[CH2:5][N:4]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])=[O:1]

Participants

6

Reactant 4

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium Bicarbonate2×HCID 21867204Cyclohexane ethylacetateHCID 59396006HCID 59396006, compound

Product 1

HCID 59396019HCID 59396019, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of phenylmethyl (1S,4S,6S)-4-(hydroxymethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate D9 (0.447 g) in DCM (13 ml) was added NaHCO3 (0.575 g, 6.84 mmol) and Dess-Martin periodinane (0.798 g, 1.882 mmol) and stirred at room temperature. TLC (Cyclohexane/EtOAc 1/1,2,4-dinitrophenylidrazine) showed the absence of starting material, so a solution of saturated NaHCO3/5% Na2S2O3 (60 ml) and DCM (10 ml) were added to the reaction mixture and it was left stirring for 30 minutes. The aqueous phase was back extracted with DCM (3×10 mls) and the biphasic system was passed through a phase separator cartridge. The organic solvent was evaporated under reduced pressure to yield a yellowish oil purified via Biotage SP4 (silica gel, SNAP 25 g; Cy/EtOAc, 25 CV from 1/0 to 7/3). Collected fractions gave the title compound D10 (0.370 g). MS: (ES/+) m/z: 260 (M+1), C15H17NO3 requires 259. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.50-9.38 (m, 1 H), 7.48-7.18 (m, 5 H), 5.19-4.93 (m, 2 H), 4.31-3.83 (m, 2 H), 3.28-2.90 (m, 1 H), 2.30-2.15 (m, 1H), 1.77-1.30 (m, 1 H), 1.21-0.84 (m, 2 H), 0.56-0.75 (m, 1 H), 0.22-0.03 (m, 1 H).

Workup

  1. waitwas left
  2. stirringstirring for 30 minutes
  3. extractionThe aqueous phase was back extracted with DCM (3×10 mls)
  4. customThe organic solvent was evaporated under reduced pressure
  5. customto yield a yellowish oil
  6. custompurified via Biotage SP4 (silica gel, SNAP 25 g; Cy/EtOAc, 25 CV from 1/0 to 7/3)

Sources & evidence

ORD record
ord-0f51f94b602e4227b7fcf2ecd69c3e3b
Source dataset
uspto-grants-2012_03
Patent number
US08133908B2

Reaction notes

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