Sodium Bicarbonate → HCID 25142821, compound
Reaction equation
[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].[OH:19][C@@H:20]1[CH2:37][CH2:36][C@@:35]2([CH3:38])[C@@H:22]([CH2:23][CH2:24][C@@H:25]3[C@@H:34]2[CH2:33][CH2:32][C@@:30]2([CH3:31])[C@H:26]3[CH2:27][CH2:28][C:29]2=[S:39])[CH2:21]1.C([O-])(O)=O.[Na+]>C1COCC1>[OH:19][C@@H:20]1[CH2:37][CH2:36][C@@:35]2([CH3:38])[C@@H:22]([CH2:23][CH2:24][C@@H:25]3[C@@H:34]2[CH2:33][CH2:32][C@@:30]2([CH3:31])[C@H:26]3[CH2:27][CH2:28][C@@H:29]2[SH:39])[CH2:21]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A 1.0 M solution of lithium tri-t-butoxy aluminum hydride in THF (6.27 mL, 6.27 mmol) was added in a dropwise manner to a solution of 3α-hydroxy-5α-androstan-17-thione (0.64 g, 2.09 mmol) in THF (60 mL) at 0° C. under N2. The solution was allowed to stir for 2 h at 0° C. and then another 2 h at room temperature. Saturated NaHCO3 (75 mL) was added and the slurry was extracted with CH2Cl2 (3×100 mL). The organics were combined, dried (MgSO4), and concentrated under reduced pressure. The resulting white solid was recrystallized from heptane to provide a white powder (0.61 g, 95%). mp. 169-170° C. 1H-NMR (300 MHz, CDCl3) δ 0.70 (s, 3H), 0.79 (s, 3H), 0.80-1.70 (m, 23H), 2.16-2.18 (m, 2H), 2.58-2.69 (dd, J=9, 18 Hz, 1H), 2.90-3.00 (dd, J=9, 9 Hz, 1H), 4.06 (m, 1H). Elemental Anal. for C19H32OS Calcd. C, 73.97; H, 10.45; S, 10.39. Found. C, 73.82; H, 10.73; S, 10.28.
Workup
- customanother 2 h
- customat room temperature
- extractionthe slurry was extracted with CH2Cl2 (3×100 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated under reduced pressure
- customThe resulting white solid was recrystallized from heptane
Sources & evidence
- ORD record
- ord-edd5729be8714ff3b971f15213f3592d
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575375B2
Reaction notes
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