CO[AlH-](OC)OC.[Li+].C(B(C(CC)C)C(CC)C)(CC)C.C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[C:36]([CH:40]1[CH2:45][CH2:44][C:43](=[O:46])[CH2:42][CH2:41]1)([CH3:39])([CH3:38])[CH3:37]>O1CCCC1>[C:36]([C@@H:40]1[CH2:41][CH2:42][C@H:43]([OH:46])[CH2:44][CH2:45]1)([CH3:39])([CH3:37])[CH3:38]To 5 ml. of 1.0M lithium trimethoxyaluminohydride in tetrahydrofuran, under nitrogen, there is added 1.25 ml. of tri-sec-butylborane. After 30 minutes, the flask, which now contains a solution of lithium tri-sec-butylborohydride, is cooled to -78° C. and 1.25 ml. of a 2.0M solution of 4-tert-butylcyclohexanone is introduced. The reaction mixture is stirred for 3 hours before it is hydrolyzed at 25° C. and then oxidized to give 96.5% of cis-4-tert-butylcyclohexanol and 3.5% of the trans-compound.
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