Sodium borohydride → 5-chloro-4-(4-ethylbenzyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)phenol

HRID 1713594Notes

Reaction equation

HRID 1713594 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@:10]21[C:43]1[CH:44]=[C:45]([CH2:49][C:50]3[CH:55]=[CH:54][C:53]([CH2:56][CH3:57])=[CH:52][CH:51]=3)[C:46]([Cl:48])=[CH:47][C:42]=1[O:41][C@H:40]2[OH:58])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C1COCC1>[Cl:48][C:46]1[C:45]([CH2:49][C:50]2[CH:55]=[CH:54][C:53]([CH2:56][CH3:57])=[CH:52][CH:51]=2)=[CH:44][C:43]([C@@:10]2([CH2:40][OH:58])[C@H:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C@@H:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@H:13]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[O:11]2)=[C:42]([OH:41])[CH:47]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 68792761HCID 68792761, compound

Product 1

HCID 687937135-chloro-4-(4-ethylbenzyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)phenolYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 27 (100 mg, 0.125 mmol) in anhydrous THF (2 mL) under an argon blanket was added sodium borohydride (23.7 mg, 0.627 mmol). The resulting mixture was stirred for 2 hours, after which it was quenched with MeOH (1 mL) and AcOH (0.5 mL), followed by partitioning between water and EtOAc. The organic phase was dried over Na2SO4, filtered, and evaporated. The residue was loaded onto a preparatory TLC plate and eluted with 15% EtOAc in petroleum ether to give 28 (92 mg, 92% yield). 1H NMR (300 MHz, CDCl3) δ 8.64 (s, 1H), 7.15-7.35 (m, 16H), 7.07-7.14 (m, 3H), 6.91-6.99 (m, 7H), 4.78-4.82 (m, 3H), 4.62 (d, J=12.0 Hz, 1H), 4.31-4.48 (m, 4H), 4.15 (dd, J=4.2, 13.2 Hz, 1H), 3.81-4.03 (m, 7H), 3.74 (d, J=10.2 Hz, 1H), 3.63 (dd, J=2.3, 10.2 Hz, 1H), 2.53 (q, J=7.5 Hz), 1.66 (t, broad, J=5.4 Hz, 1H, OH?), 1.16 (t, J=7.5 Hz, 3H). LC/MS m/z 822 (M+Na).

Workup

  1. customafter which it was quenched with MeOH (1 mL) and AcOH (0.5 mL)
  2. customby partitioning between water and EtOAc
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. washeluted with 15% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-81d8d8150bfe45889e377f7533eca4ea
Source dataset
uspto-grants-2010_09
Patent number
US07795228B2

Reaction notes

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