Sodium Thiosulfate → trans-4-[(Boc-amino)methyl]cyclohexanecarbaldehyde

HRID 2277012Notes

Reaction equation

[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][OH:16])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH:9]1[CH2:10][CH2:11][CH:12]([CH:15]=[O:16])[CH2:13][CH2:14]1)([CH3:2])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: -78 °C

Procedure

(4-Hydroxymethyl-cyclohexylmethyl)-carbamic acid tert-butyl ester (965 mg, 4.0 mmol) was dissolved in DCM (20 ml) and cooled down to −78° C. Dess Martin reagent (2.52 g, 6.0 mmol) was dissolved in DCM (30 ml) and added slowly to the stage 2 alcohol in solution. The reaction mixture was then stirred at r.t. for 3 h. The resulting solution was poured into a vigorously stirred saturated NaHCO3 and Na2S2O3 solution (1:1, 100 ml). The organic layer was separated and washed with brine, dried over magnesium sulfate and evaporated to dryness to yield the product (786 mg, 82% yield). 1H NMR (300 MHz, CDCl3), δ: 0.83-1.01 (2H, m, CH2), 1.15-1.24 (2H, m, CH2), 1.34 (9H, s, Boc), 1.75-1.88 (2H, m, CH2), 1.90-2.00 (2H, m, CH2), 2.05-2.18 (1H, m, CH), 2.93 (2H, t, J=6.4 Hz, CH2NH), 4.53 (1H, br. s, CHCHO), 9.55 (1H, s, CHO)

Workup

customThe organic layer was separated
washwashed with brine
dry with materialdried over magnesium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-6398c3e64aba4264a08f2b0cbdf19eb4
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133104B2

Reaction notes

Loading…